Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
  • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
  • C07C69/12—Acetic acid esters
  • C07C69/14—Acetic acid esters of monohydroxylic compounds
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
  • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
  • C07C69/78—Benzoic acid esters
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
  • Y10S8/92—Synthetic fiber dyeing
  • Y10S8/922—Polyester fiber

Definitions

• the present invention relates to benzophenone ether esters, processes for their preparation, their use for improving the light stability of polyester dyeings and a dyeing process and dye preparations.
• benzophenone ether esters which are used for protecting plastics, such as, for example, polyacrylic esters, polymethacrylic esters, polystyrene and ABS polymers, against the effect of UV light are disclosed in EP 182 056.
• the object of the present invention is to provide compounds which lead to an improvement in the light fastness of dyeings on polyester materials, without reduction in the exhaustion of the dye onto the fiber and the depth of shade and brilliance of the dyeing.
• R 1 and R 4 independently of one another, are (C 1 -C 6 )-alkyl, cyano, fluorine, chlorine, bromine, trifluoromethyl or hydrogen;
• R 2 and R 3 independently of one another, are (C 1 -C 6 )-alkyl or hydrogen;
• x and y independently of one another, are 0, 1 or 2 and
• R 5 represents (C 1 -C 12 )-alkyl; (C 3 -C 8 )-cycloalkyl; (C 1 -C 12 )-alkyl or (C 3 -C 8 )-cycloalkyl, each of which is substituted by (C 1 -C 6 )-alkoxy, (C 2 -C 7 )-alkoxycarbonyl, amino, (C 1 -C 6 )-alkylamino, di-(C 1 -C 6 )-alkylamino, hydroxyl, cyano, fluorine, chlorine, bromine, trifluoromethyl or nitro; phenyl or phenyl substituted by (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, (C 2 -C 7 )-alkoxycarbonyl, amino, (C 1 -C 6 )-alkylamino, di-(C 1 -C 6 )-alkylamin
• alkyl, alkoxy, alkoxycarbonyl, alkylamino and dialkylamino radicals can be straight-chain or branched.
• the radicals R 1 and R 4 can be in the ortho, meta or para position relative to the carbonyl group. Where x or y is 2, the substituents can be in the 1,2-, 1,3- or 1,4-position relative to one another.
• radicals R 2 and R 3 can be bound to all three free positions of the six-membered ring.
• R 1 and R 4 independently of one another, are hydrogen, (C 1 -C 3 )-alkyl, cyano, chlorine or trifluoromethyl,
• R 2 and R 3 independently of one another, are hydrogen or (C 1 -C 3 )-alkyl
• x and y independently of one another, are 0 or 1 and
• R 5 is (C 1 -C 4 )-alkyl; cyclopentyl, cyclohexyl; (C 1 -C 4 )-alkyl, cyclopentyl or cyclohexyl, each of which is substituted by (C 1 -C 4 )-alkoxy, (C 2 -C 5 )-alkoxycarbonyl, amino, (C 1 -C 4 )-alkylamino, di-(C 1 -C 4 )-alkylamino, hydroxyl, cyano, fluorine, chlorine, bromine, trifluoromethyl or nitro; phenyl or phenyl which is substituted by (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, (C 2 -C 5 )-alkoxycarbonyl, amino, (C 1 -C 14 )-alkylamino, di-(C 1 -C 4 )-alkylamin
• R 1 , R 2 , R 3 and R 4 are hydrogen
• R 5 is methyl or phenyl.
• the compounds according to the invention of the general formula I can be prepared by reacting a compound of the general formula II ##STR3## in which R 1 , R 2 , R 3 , R 4 , x and y are as defined above, with a compound of the general formula III ##STR4## in which X represents hydroxyl, halogen, (C 1 -C 4 )-alkoxy or --OCOR 5 and R 5 is as defined above.
• the reaction is advantageously carried out at temperatures of 0° to 150° C., particularly preferably at 50° to 120° C.
• the reaction is carried out in an inert organic solvent.
• Suitable solvents of this type are in particular aromatic hydrocarbons having 6 to 8 carbon atoms, which may be substituted by a halogen atom, for example by a chlorine atom, or aliphatic halohydrocarbons, for example chlorohydrocarbons having 1 to 2 carbon atoms.
• Particularly preferred solvents are benzene, toluene, xylene, chlorobenzene, chloroform, tetrachloromethane and 1,2-dichloroethane.
• the solvent is preferably used in amounts of 1 to 10 liters, particularly preferably 5 to 8 liters, per mole of the compound of the general formula I.
• an inorganic or organic acid being particularly suitable.
• Organic sulfonic acids such as, for example, p-toluenesulfonic acid, are preferred.
• Organic sulfonic acids containing halogen atoms, in particular fluorine atoms, such as, for example, trifluoromethanesulfonic acid, are par-ticularly preferred.
• Acid ion exchangers are also suitable as acid catalysts.
• the catalyst is preferably used in an amount of 1 to 10, particularly preferably 3 to 6, percent by weight, relative to the compound of the general formula II.
• the compound of the general formula III is preferably used in an excess of up to 10 mol per mole of compound of the general formula II. An excess of 3 to 8 mol is particularly preferred.
• the compounds of the general formula III are carboxylic acids or carboxylic acid derivatives which are commercially available and/or preparable by methods known to one skilled in the art.
• carboxylic acids of this type are aliphatic carboxylic acids, such as acetic acid, propionic acid or butyric acid and aromatic carboxylic acids, such as benzoic acid.
• R 6 is hydrogen, phenyl, (C 1 -C 12 )-alkyl or cyano and R 7 and R 8 , independently of one another, are hydrogen, (C 1 -C 8 )-alkyl, phenyl or phenyl substituted by (C 1 -C 4 )-alkyl or (C 1 -C 4 )-alkoxy or together form an alkylene radical having 4 or 5 carbon atoms, are highly suitable for this purpose.
• the present invention also relates to the use of a compound of the general formula I ##STR6## in which R 1 and R 4 , independently of one another, are (C 1 -C 6 )-alkyl, cyano, fluorine, chlorine, bromine, trifluoromethyl or hydrogen;
• R 2 and R 3 independently of one another, are (C 1 -C 6 )-alkyl or hydrogen;
• x and y independently of one another, are 0, 1 or 2 and
• R 5 represents (C 1 -C 12 )-alkyl; (C 3 -C 8 )-cycloalkyl; (C 1 -C 12 )-alkyl or (C 3 -C 8 )-cycloalkyl, each of which is substituted by (C 1 -C 6 )-alkoxy, (C 2 -C 7 )-alkoxycarbonyl, amino, (C 1 -C 6 )-alkylamino, di-(C 1 -C 6 )-alkylamino, hydroxyl, cyano, fluorine, chlorine, bromine, trifluoromethyl or nitro; phenyl or phenyl substituted by (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, (C 2 -C 7 )-alkoxycarbonyl, amino, (C 1 -C 6 )-alkylamino, di-(C 1 -C 6 )-alkylamin
• the present invention also relates to a process for the dyeing of textile polyester material using disperse dyes, characterized in that the dye bath contains, for improving the light fastness of the dyeing, at least one compound of the general formula I, not only the compounds according to the invention of the general formula I but also the compounds of the general formula I disclosed in EP 182 056, in which R 5 represents the group A, being included.
• Textile polyester material is understood to mean in particular structures such as, for example, fibers, yarns, woven fabrics, knitted fabrics and films made of, for example, polyethylene terephthalates, polybutylene terephthalates or polyethylene glycol terephthalates.
• the disperse dyes used are preferably commercially available disperse dyes, such as, for example, azo, anthroquinone, methine, quinophthalone or coumarin dyes.
• Dyeing can take place, for example, by the so-called exhaust method under HT conditions, at the boiling temperature with the addition of carrier or even by the so-called thermosol method.
• the dyeing processes mentioned are known to one skilled in the art and described in the relevant literature.
• the dye baths contain the compounds of the general formula I in amounts of preferably 0.1 to 10, particularly preferably 0.3 to 5, percent by weight, relative to the textile material to be dyed.
• the compounds of the general formula I can be added to the dye baths, for example, as powders, spray-dried/redispersible, or as liquid preparation in the form of a dispersion.
• the compounds of the general formula I are already present in the dye preparations from which the dye baths are produced.
• the present invention also relates to a dye preparation characterized in that it contains at least one compound of the general formula I, not only the compounds according to the invention of the general formula I but also the compounds of the general formula I disclosed in EP 182 056, in which R 5 represents the group A, being included.
• the dye preparations according to the invention are liquid or pulverulent disperse dye preparations containing the compounds of the general formula I preferably in amounts of 1 to 50 percent by weight, particularly preferably 1 to 30 percent by weight.
• the dye content is preferably 15-40 percent by weight, particularly preferably 20-30 percent by weight.
• the dye preparations are prepared by milling the dye in the presence of one or more compounds of the general formula I, one or more dispersants or one or more emulsifiers and, if desired, in the presence of further auxiliaries together in suitable mills.
• suitable mills are ball or sand mills.
• the milling process is carried out at 0° to 100° C., preferably at 20° to 70° C.
• the milling process must be followed by spray-drying.
• the compounds of the general formula I can also be added after milling, provided they are thoroughly stirred in.
• suitable dispersants are anionic or nonionic dispersants, which may also be used together.
• anionic dispersants are condensation products of aromatic sulfonic acids with formaldehyde, in particular condensation products of alkylnaphthalenesulfonic acids with formaldehyde, condensation products of substituted or unsubstituted phenol, naphthalene- or naphtholsulfonic acids with formaldehyde and sodium bisulfite, alkali metal salts of condensation products with formaldehyde and urea and alkali metal salts of lignosulfonic acids.
• Alkyl- or alkylarylsulfonates and alkylarylpolyglycol ether sulfates and in particular neutralized esters of an oxethylated novolak are examples of nonionic dispersants or emulsifiers.
• nonionic dispersants or emulsifiers are ethylene oxide or propylene oxide together with alkylatable compounds, such as, for example, fatty alcohols, fatty amines, fatty acids, phenols, alkylphenols, arylalkylphenols, arylalkylarylphenols and carboxamides, such as, for example, addition products of 5 to 10 ethylene oxide units with C 8 -C 10 -alkylphenols.
• the dispersants mentioned are present in liquid dye preparations in an amount of 15-40 percent by weight, preferably 20-30 percent by weight, and in pulverulent dye preparations in an amount of 20-45% by weight.
• the dye preparations according to the invention can also contain further auxiliaries, for example those acting as oxidizing agents, such as, for example, sodium m-nitrobenzenesulfonate or fungicides, such as, for example, sodium o-phenolphenolate[sic] and sodium pentachlorophenolate.
• Dye mixtures which are formulated as powders moreover additionally contain other auxiliaries, such as, for example, wetting or dedusting agents.
• the dye preparations contain the auxiliaries mentioned in amounts of 0-5 percent by weight, preferably 0-2 percent by weight.
• Dyeings which are obtained by the dyeing process according to the invention i.e. in the presence of compounds of the general formula I, do not differ or differ only insignificantly from those obtained without addition of the compounds of the general formula I with respect to their hue. However, they are distinguished by a substantially higher light fastness, in particular also hot light fastness. Thus, even the high demands made on dyeings in the automotive sector (seat covers, parcel shelves, and the like) are met and even exceeded.
• a dye bath comprising 1500 parts of water, 0.6 part of a dye mixture of
• ®Dispersogen A (dispersant from Hoechst AG, Frankfurt, West Germany) and 1.5 parts of the compound from a) is brought to a pH of 4.5-5 with acetic acid.
• a polyester velour 100 parts are dyed in a dye bath which is analogous to that from Example 1b) but contains 1.5 parts of the compound from Example 2a and a dye mixture of 0.43 part of Disperse Yellow 51, 0.46 part of a red mixture as in Example 1b) and 0.17 part of Disperse Blue 77.
• the product thus obtained has a melting point of 168°-169° C. and a purity of 99% (HPLC). UV, IR and NMR spectra correspond to the compound mentioned.
• 100 parts of a polyester knitted fabric are dyed in a dye bath analogous to that from Example 1b) but containing 2 parts of the compound from Example 3a) and a dye mixture of 0.46 part of Disperse Yellow 42, 0.17 part of a red mixture as in Example 1b) and 0.17 part of a blue mixture as in Example 1b).

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Coloring (AREA)
• Mechanical Operated Clutches (AREA)
• Braking Arrangements (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
• Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Applications Claiming Priority (2)

Publications (1)

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Cited By (23)

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Citations (3)

• 1989
  • 1989-09-13 DE DE3930516A patent/DE3930516A1/de not_active Withdrawn
• 1990
  • 1990-09-06 DK DK90913388.6T patent/DK0491764T3/da active
  • 1990-09-06 JP JP2512369A patent/JPH05500663A/ja active Pending
  • 1990-09-06 KR KR1019920700561A patent/KR100200993B1/ko not_active IP Right Cessation
  • 1990-09-06 DE DE59008379T patent/DE59008379D1/de not_active Expired - Fee Related
  • 1990-09-06 EP EP90913388A patent/EP0491764B1/de not_active Expired - Lifetime
  • 1990-09-06 BR BR909007640A patent/BR9007640A/pt not_active Application Discontinuation
  • 1990-09-06 US US07/838,765 patent/US5244476A/en not_active Expired - Lifetime
  • 1990-09-06 ES ES90913388T patent/ES2067758T3/es not_active Expired - Lifetime
  • 1990-09-06 WO PCT/EP1990/001493 patent/WO1991004243A1/de active IP Right Grant

Patent Citations (3)

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